Ep 234 | Jesse Draper

Written By Yasmin Nouri

Overcoming Imposter Syndrome & Stepping Into Your Power

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Jesse Draper is the Founding Partner of Halogen Ventures, a venture capital firm focused on early-stage investing in consumer tech companies led by female and co-ed teams.

With women making up to 80 percent of household purchasing decisions, Jesse and her team are betting big on early-stage, female-founded companies with billion-dollar potential. Jesse is a fourth generation venture capitalist as well as the creator and host of the Emmy-nominated television series, The Valley Girl Show.

She is a fierce advocate for investing in women and the opportunity for using technology and innovation to solve some of the biggest issues facing women and families today. After creating Halogen Ventures in 2015, she now has more than 70 companies in her portfolio, including theSkimm, Babylist, ThirdLove, and The Flex Company.

Jesse was listed by Marie Claire Magazine as one of the ‘50 Most Connected Women in America’ and she is also a regular investor and tech personality on Cheddar, CNBC, and CNN.

In this episode, we have a candid conversation about why Jesse didn’t think she could be a venture capitalist and how she overcame her own fears and beliefs about imposter syndrome, and she shares her advice for anyone looking to manage burnout: delegate and make time for rest. We also get a behind-the-scenes look at what investors are looking for, from founder traits to the biggest mistakes that founders make, and so much more.

Show Notes:

  • Starting on the topic of rejection; why a ‘no’ isn’t necessarily a bad thing. [3:40]

  • How Jesse’s upbringing shaped her as a fourth generation venture capitalist. [7:52]

  • Her perception of success in her 20s and how it evolved with entrepreneurship. [12:33]

  • Find out why Jesse believes more women should prioritize networking. [20:04]

  • Overcoming her fears and beliefs about imposter syndrome; just try it! [24:27]

  • Jesse’s advice for managing burnout: delegate and make time to rest and plan. [28:30]

  • Learn more about her experience of fundraising while pregnant and during COVID. [35:50]

  • Three mistakes women are making when raising money: not showing confidence, overcomplicating the pitch, and underselling themselves. [38:30]

  • What investors look for, from a willingness to pivot to an ability to problem solve. [41:33]

  • Some of the red flags Jesse cautions founders against, including the tendency to overpromise and underdeliver. [45:50]

  • Jesse’s suggestions for women to feel more empowered when it comes to money. [50:10]

  • Two simple ways to take control: do it yourself and put your money to work. [53:47]

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Ep 233 | Yasmin Nouri and Kaya Purohit